A beginner’s guide to anal

Jessie Mathewson 27 November 2016

While much of the advice in this column is broadly applicable, it is written from the perspective and experience of the receiver in a heterosexual couple.

Several people have approached me requesting that I write a column on “anal tips”. It’s a sore topic. Literally – my butt kind of hurts just thinking about it. But since writing a sex column is realistically the closest I will ever come to public service (and I’ve always aimed to please), I have complied below advice so foolproof, so latex-tight that you can booty bash to your heart’s content, should you so wish. I hope you’re s(h)itting comfortably.

Before we begin – a note to my parents, my future employers, and my future self. Please forgive me for what you are about to read: it was done in the service of friends. Even as someone who splashes her sexploits in print and online for the world to see, I feel like I’m crossing some kind of line writing about anal. 

Let’s take a moment to think about why that might be. The fact that I’m so quick in this instance to defend whatever shreds may be left of my honor after an entire year of aggressively sexually oversharing is so indicative of the stigma that surrounds anal – specifically, receiving and not giving. But let’s leave the mock horror at the (back) door, shall we? Studies (like those in the British Medical Journal and the Journal of Sexual Medicine) clearly demonstrate that more people than ever before are practicing anal sex, especially among women aged between 20-30. A third of heterosexual couples practice it. 

In spite of this, there are a hell of a lot of misconceptions about the kind of people who are down for a stay in booty town. That we’re easy – “conquestable” somehow – because anal sex is some kind of weirdly fetishized sexual achievement for lad-types. There’s definitely a power aspect to anal: it’s actually probably something I enjoyed more than the actual sensation. This is, of course, linked to the taboo that arbitrarily surrounds it. Hopefully by talking about it like it’s not some weird thing to be ashamed of I can weaken that a little. This is my first piece of advice: make sure you or your partner(s) want anal for the right kind of reasons. 

Despite common misconception, it really should not hurt lots the first time (the same is true of vaginal sex!). The first few times it will feel pretty weird and maybe uncomfortable – it’s an unusual sensation – but it shouldn’t be something that you feel you have to endure. Lube is your butts best friend, but avoid brands that market themselves as “anal ease” like the plague: they’ve got numbing agents in them. Frankly having pins and needles in your asshole should be enough to put anyone off, but on a more practical note they also can make you unaware of any damage that might be done in being a little too vigorous. 

A word of warning: if you try and hop right up in there like they do in porn movies it’s going to end horribly. It’s kind of like thinking you somehow know how to drive after completing a record lap of Yoshi Falls. Bad vaginal sex usually just means it was a bit pathetic and you didn’t come; bad anal sex doesn’t really bear thinking about. It’s worth noting that the levels of cleanliness in porn don’t happen by accident; in some cases these people starve and/or give themselves enemas before anal sex. You are not expected to do this: if your partner wants the honor of putting their dick up your ass, your (inevitable) poo becomes their problem. Embrace your humanity. 

Before attempting anal, not only make sure that you’ve warmed up first but that you’ve practiced things like rimming and fingers multiple times (pro tip: put a condom over your finger to protect your manicure) so that you know you like and are used to the sensation. You can also get “anal training kits” with increasing sizes of butt plugs if you like the sensation but aren’t game for penile penetration. 

Some vagina-owners report being able to come from anal, but it’s super rare. It’s usually a sensation best in combination with clitoral stimulation (try lying on your front with a vibrator below you). Men, as I’m sure you know, have their prostate gland just before the rectum: if you insert a finger and move in a beckoning motion towards yourself you should be able to feel it. 

In my experience, for the first few times anal just feels a bit odd as opposed to genuinely unpleasant. I’m definitely not in any hurry to try it again, but that’s a personal preference and shouldn’t deter anyone. If it’s genuinely painful, it’s up to you to decide if it’s worth some practice to normalize it a bit. As with many first things, the first few times will probably be a bit shit. There is, sadly, the added complication that there might also be a little bit of shit.